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Lithium hydroxide, monohydrate → {6-Fluoro-4-[4-(4-fluoro-phenyl-sulfamoyl)-phenyl]-3-methyl-naphthalen-2-yl}-acetic acid

HRID 1468426
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1468426
O.[OH-].[Li+].C[O:5][C:6](=[O:37])[CH2:7][C:8]1[C:17]([CH3:18])=[C:16]([C:19]2[CH:24]=[CH:23][C:22]([S:25](=[O:35])(=[O:34])[NH:26][C:27]3[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=3)=[CH:21][CH:20]=2)[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([F:36])[CH:14]=2)[CH:9]=1.C1COCC1.O>CCCCCC>[F:36][C:13]1[CH:14]=[C:15]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([CH2:7][C:6]([OH:37])=[O:5])[C:17]([CH3:18])=[C:16]2[C:19]1[CH:20]=[CH:21][C:22]([S:25](=[O:34])(=[O:35])[NH:26][C:27]2[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=2)=[CH:23][CH:24]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 168937Lithium hydroxide, monohydrateHCID 21881883Oxolane--water (1/1)HCID 86695014{6-Fluoro-4-[4-(4-fluoro-phenylsulfamoyl)-phenyl]-3-methyl-naphthalen-2-yl}-acetic acid methyl ester

Produkt 1

HCID 71711445{6-Fluoro-4-[4-(4-fluoro-phenyl-sulfamoyl)-phenyl]-3-methyl-naphthalen-2-yl}-acetic acidAusbeute 77,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8058
Hexane
Lösungsmittel

Versuchsvorschrift

Lithium hydroxide monohydrate (0.08 g, 0.19 mmol) was added to a stirred solution of {6-fluoro-4-[4-(4-fluoro-phenylsulfamoyl)-phenyl]-3-methyl-naphthalen-2-yl}-acetic acid methyl ester (0.023 g, 0.047 mmol) in a 3:1 mixture of THF—H2O mixture (4 mL). The reaction mixture was stirred for 16 hours at room temperature. The reaction mixture was concentrated to remove THF, and the crude material was diluted with water, acidified [pH˜2] with a 6 N aqueous solution of hydrochloric acid. The mixture was extracted twice with ethyl acetate. The collected organic layers were washed with water and brine, dried over anhydrous Na2SO4, and concentrated under reduced pressure to give the crude product. Trituration with hexane afforded {6-fluoro-4-[4-(4-fluoro-phenyl-sulfamoyl)-phenyl]-3-methyl-naphthalen-2-yl}-acetic acid (0.017 g, 76%) as a solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.45 (br. s, 1 H), 7.99 (dd, J=9.20, 6.40 Hz, 1 H), 7.89 (s, 1 H), 7.85 (m, J=8.30 Hz, 2 H), 7.41 (d, J=8.31 Hz, 2 H), 7.34-7.38 (m, 1 H), 7.10-7.15 (m, 3 H), 6.50 (dd, J=11.00, 3.20 Hz, 1 H), 3.83 (s, 2 H), 2.01 (s, 3 H). MS calcd. for C25H18F2NO4S [(M−H)−] 466, obsd. 466.0.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated
  2. customto remove THF
  3. additionthe crude material was diluted with water
  4. extractionThe mixture was extracted twice with ethyl acetate
  5. washThe collected organic layers were washed with water and brine
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated under reduced pressure
  8. customto give the crude product

Quellen und Nachweise

ORD-Eintrag
ord-354885b4b5af448298e61b5c2331591e
Quelldatensatz
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09000044B2

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